How to figure out what to do with your life

Link: https://www.julian.com/blog/life-planning

Intro

Julian was a Y-combinator startup founder, but I knew him because of his high-quality writing.

In this article, Julian shared his mental process when deciding what he should pursue next: startup or writing.

The title of the article is a big claim, but I think it deserves it.

Highlights

Without self-reflection, we ride the momentum of whatever we're already doing and whatever we stumble across. This means we work on the wrong things by default, because our core values shift over time and they're often not what they used to be.

In Socrates' words: "The unexamined life is not worth living"

First, the author listed the values he cares about when pursuing a new project:

* Knowledge— Do you become more knowledgeable and skilled from it?
* Adventure— Do you accrue novel, memorable experiences?
* Fame— Do you build an audience you can later leverage?
* Power— Do you acquire resources and connections?
* Money— Do you increase your financial wealth?
* Exercising Talent— Do you leverage your skill and creativity?
* Human Connection— Do you bond with others?

It took 15 minutes to realize that those are the things I care about. What's crazy is that I didn’t do this exercise until I was 27.

I don't think I can make such a list in 15 mins. He summarised it pretty well. Of course, this list won't cover everyone's values. But for me, it's quite hard to articulate what's missing.

I ordered the values by what I care most about today. Then I drew checkmarks next to those that were fulfilled by startups and writing.

After this process, writing won. Some values startup promises are ranked low by the author, while writing brings the top-ranked ones. But this is not the end of the story yet.

But I still can't shake the emotional desire to pursue startups.

I recently discovered that framework. It's called Regret Minimization. Eureka.

It boils down to this: What choices can you make today that minimize the regret you'll feel as an 80-year-old looking back on your life? When you minimize future regret, you sleep well knowing you're maximizing fulfillment.

With the Regret Minimization framework, he finally made up his mind.

Here was the eureka moment: The moment I understood that I'd be more regretful having failed to become a successful writer than a successful startup founder, I was no longer clasping onto the fading aspiration of startups. Instead, I was focused on ensuring I aged with minimal regret.

Our values change over time. It's not self-evident unless we self-assess. We self-assess by ordering our values and identifying which projects best satisfy the highest-ranked values. We then use regret minimization to overcome our bias toward past ambitions.

Next, here is some advice from the author to do this exercise effectively.

First, some people might underestimate the value of knowledge and exercising talents (i.e. being challenged):

Personal growth via knowledge accumulation is how you avoid the intellectual stagnation of most jobs—that feeling of standing still while the world passes by. Next, being challenged is how you remain intellectually engaged—the feeling that you're playing the game of life.

People fail to realize that career success isn't an end state. Success is simply having the freedom to focus on the ongoing grind you actually enjoy.

Second, people tend to overestimate the power of money:

Have you heard of hedonistic adaptation? It's the phenomenon where people revert to their baseline of happiness no matter how much more income they earn.

But what would huge amounts of money ultimately do for me? I guess it would help me fulfill more of the values I care about. I can spend money to attain Knowledge, Fame, Power, Adventure, and so on. But, if writing gets me more of those values right now... then what's the point of taking a decades-long detour to turn Money back into my preferred values?

Here's what I believe: Becoming very rich is appealing to people who've never actually achieved fulfillment. Had they felt and internalized the joy of Knowledge or Adventure, they'd shortcut to optimizing for that end goal instead.

That said, there is of course a critical importance in attaining at least a healthy baseline of income: 1. Money frees you from doing the things you don't want to do. 2. Money removes your anxiety over achieving financial stability for you and the people you care about.

Third, be aware of groupthink.

It's important to remember that the people surrounding you distort the perception of your own values.

"I’ve noticed that many people compete in games they don’t understand because they are modeling the behavior of people around them. Most common is the competition for wealth as a proxy for happiness." —Michael Seibel

Finally, the list may be different from person to person, and the ordering could change from time to time.

For many, that list will include Knowledge, Adventure, Fame, Power, Money, Exercising Talent, and Human Connection. I'm missing others that matter to you. My list isn't universal.

We fundamentally change over time, but it's not obvious that we have unless we pause to self-assess. If we're lazy and just ride life's momentum, we're likely to regret how we spend our years.

Closing Comments

I read this article for the first time more than 3 years ago. And I have tried to examine my pursuit with this framework. But I have to say, I couldn't think as clearly as the author did. It's super hard to categorize one's values into abstract concepts and rank them. It may take me some deliberate soul-searching, or just need the right moment to come 😂

The seven values summarized by the author are pretty handy. Before I can come up with something that fits me better, this framework is a good starting point when thinking about what to do next.